This invention relates to a novel method for the preparation of epoxyalcohols. More particularly, this invention is directed to the oxidation of acyclic or cyclic olefins to form the corresponding epoxyalconols in the presence of an ion-exchanged bimetallic catalyst in which the metals are valence-bonded to an anionic support. Epoxyalcohols are useful as intermediates in the preparation of glycerine and related compounds. Thus, for example, glycidol (from propylene) would give glycerine when hydrolyzed. Similarly, 1,2-epoxy-3-hydroxy-2,3-dimethylbutene can be hydrolyzed to form the corresponding substituted glycerine which could have utility as a humectant and as a trifunctional monomer in the preparation of polymers.
Cyclic olefins, such as cyclohexene, when converted to the corresponding 1,2-epoxy-3-hydroxy-cyclohexane, may be dehydrogenated to form catechol. Substituted cyclohexenes yield the corresponding epoxyalcohols which can be dehydrogenated to yield substituted dihydroxybenzenes.
This invention also relates to certain novel metal-exchanged catalysts per se which are useful in the aforedescribed epoxidation process.
Van Sickle et al, J. Catal. 19, 209 (1970), disclosed the use of cobalt-exchanged zeolites as catalysts for the unselective oxidation of olefins to form a mixture of ketones and unsaturated alcohols, along with a minor amount of epoxides in some cases. U.S. Pat. No. 3,641,066 (1972) teaches a similar process wherein molybdenum, tungsten, or vanadium-exchanged zeolite catalysts are employed in the formation of olefin epoxides. In neither case, however, the epoxy-alcohols obtained as reaction products. Finally, Belgian Patent No. 640,204 teaches the preparation of epoxyalcohols from olefins using as a catalyst system a compound derived from metals of Group IVA, VA, or VIA of the Periodic System, plus an alkylhydroperoxide and a radical initiator.